tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Name: tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate
Brand: ChemScene
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CAS No. 77215-55-5
Cat. No. CS-0046997
Purity≥96%
MDL No.None

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tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate|CS-0046997

Structure of 77215-55-5

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General Information

CAS No. 77215-55-5
Cat. No. CS-0046997
Purity ≥96%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₂N₂O₄
Molecular Weight 294.35
Synonym(s) (s)-3-Amino-2-cbz-amino-propionic acid tert-butyl ester
SMILES O=C([C@@H](NC(OCC1=CC=CC=C1)=O)CN)OC(C)(C)C

Description

tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate features a chiral (S)-configured amino acid scaffold with orthogonal protection: the amine is masked as a tert-butyl carbamate, while the α-hydroxyl group is esterified as a benzyl carbonate. This bifunctional handle enables selective deprotection and coupling in peptide synthesis, offering high stability under standard conditions and compatibility with diverse reaction environments.

Application

tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate serves as a key chiral building block for peptide synthesis and medicinal chemistry. The protected α-amino acid moiety enables efficient coupling reactions, while the benzyloxycarbonyl (Cbz) group provides orthogonal protection for the amine. This compound exhibits excellent bench stability, ease of purification, and compatibility with standard deprotection protocols, facilitating scalable synthesis of bioactive peptides and heterocyclic scaffolds.

Synthesis

Route1
- In-stock
  
  35761-26-3
- 115-11-7
- ~72%
- In-stock
  
  77215-55-5
References
- DuPont Pharmaceuticals Company Patent: US6153628 A1, 2000 ;
Route2
- 540-88-5
- In-stock
  
  35761-26-3
- ~%
- In-stock
  
  77215-55-5
References
- Polish Journal of Chemistry, , vol. 79, # 3 p. 567 - 572
Route3
- In-stock
  
  1482-97-9
- 501-53-1
- 115-11-7
- ~%
- In-stock
  
  77215-55-5
- 77255-62-0
References
- Journal of Medicinal Chemistry, , vol. 24, # 5 p. 554 - 559

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 90.65
LogP 1.5818
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Amine

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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tert-Butyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

CAS No. 77215-55-5

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